Aqueous-based cosmetic detergent compositions

ABSTRACT

IMPROVED AQUEOUS DETERGENT COMPOSITIONS FOR COSMETIC APPLICATIONS COMPRISING WATER, A SYNTHETIC ORGANIC DETERGENT, AND FROM ABOUT 1-20%, BY WEIGHT, OR AN AMMONIUM, ALKANOLAMINE OR ALKALI METAL SALT OF A MONOESTER OF A C3-C6 SATURATED ALIPHATIC DICARBOXYLIC ACID WITH A FATTY ACID ALKANOLAMIDE. THE COMPOSITONS EXHIBIT IMPROVED PROPERTIES WITH REGARD TO EMOLLIENCY, WETTING LATHERING AND THE LIKE.

United States Patent Ofice 3,703,481 Patented Nov. 21, 1972 3,703,481AQUEOUS-BASED COSMETIC DETERGENT COMPOSITIONS Graham Barker, Fair Lawn,N.J., and Herman W. Campbell, Chicago, Ill., assignors to Witco ChemicalCorporation, New York, N.Y. No Drawing. Filed- Jan. 25, 1971, Ser. No.109,614 Int. Cl. Clld 1/20 US. Cl. 252546 11 Claims ABSTRACT OF THEDISCLOSURE This invention relates to improved detergent and surfactantcompositions. More particularly, this invention relates to improvedaqueous-based cosmetic detergent compositions having improvedcharacteristics with regard to emolliency, wetting, lathering, hairmanageability, counter-irritancy and the like.

Surfactant compositions, including cosmetic surfactant compositions suchas shampoos, shaving creams, skin cleansing compositions and the like,containing various derivatives of polycarboxylic acids are known to theart and are disclosed, for example, in US. Pats. No. 2,452,- 043, issuedOct. 26, 1948 to Lawrence H. Flett; No. 2,490,459, issued Dec. 6, 1949to Werner Max Lilienfeld; -No. 2,562,154, issued July 24, 1951 to EmilA. Vitalis; and 2,878,190, issued Mar. 17, 1959 to Vladimir Dvorkovitzet al. Compounds therein disclosed include, among others, succinicacids, sulfosuccinic acids, sulfosuccinamic acids, esters, sulfosuccinicesters of fatty alkanolamides and salts thereof and various derivativesthereof, and are reported as useful in surfactant compositions,particularly shampoos. However, the aforesaid have numerous deficienciespreventing their use in a wide variety of aqueous-based surfactantcompositions as opposed to the fatty alkanolamide monoester saltadditives more particularly described herein.

In accordance with the present invention, there have been discoveredimproved aqueous based cosmetic detergent compositions comprising water,a member of the group of synthetic anionic, nonionic and cationicorganic detergents and compatible mixtures of same, and from about 1 to20%, preferably 3 to by weight, of a member of the group of ammonium, C-C alkanolamine and alkali metal salts of the monoester of a C -Csaturated, unsubstituted, aliphatic dicarboxylic acid with fatty acidmonoand dialkanol-amides wherein the alkanol portion contains up to 8carbon atoms.

The compositions of the present invention contain, as an essentialingredient, from about 1 to 20%, by weight, of an aforesaid salt of amonoester of a C -C saturated, aliphtic dicarboxylic acid such assuccinic, malonic, glutaric or adipic acid with a fatty acidalkanolamide.

The fatty acid alkanolamides are well known to the art and generallycomprise those prepared from saturated and unsaturated aliphaticmonocarboxylic acids containing from about 8 to 22 carbon atoms andpreferably those containing from about 10 to 18 carbon atoms. Exemplaryfatty acids are caprylic, capric, lauric, myristic, palmitic, stearic,arachidic, behenic, oleic, linoleic and eleostearic acids and the like,as well as mixed fatty acids such as tall oil fatty acids, hydrogenatedtallow fatty acids, coconut oil fatty acids and vegetable fatty acidssuch as are derived from cottonseed and soybean oil, as well as rosinfatty acids. The alkanolamines which may be condensed with the aforesaidfatty acids comprise both monoand dialkanolamines containing up to 8carbon atoms and are exemplified by monoethanolamine, diethanolamide,isopropanolamine, diisopropanolamine, butanolamine, dibutanolamine,diisobutanolamine and the like. These fatty acid alkanolamides may beprepared by various well known techniques such as by condensingequimolar quantities of fatty acid with alkanolamine, or by condensing amolar excess of alkanolamine with fatty acid or by reacting a fatty acidester with alkanolamine, or by oxyalkylating, such as oxyethylating, theamide of the fatty acid. Particularly preferred fatty alkanolamides arefatty acid monoalkanolamides, particularly monoethanolamides.

The monoesters are prepared, for instance, by reacting appropriatesubstantially stoichiometric quantities of C -C aliphatic saturateddicarboxylic acids with the aforesaid fatty acid alkanolamides in orderto prepare fatty acid alkanolamidedicarboxylic acid monoesters havingone free COOH available for salt formation. The fatty acid alkanolamideis preferably esterified with succinic acid. The monoester salts may bethe water-soluble ammonium, C -C alkanolamine such as ethanolamine,diethanolamine, triethanolamine, isopropanolamine, diisopropanolamineand the like, or alkali metal salts, of the aforesaid monoesters of thefatty acid alkanolamides with dicarboxylic acids. Preferably themonoester salt will be the sodium salt.

The aforesaid salts of fatty acid alkanolamide-dicarboxylic acidmonoesters are employable in a wide variety of aqueous-based cosmeticdetergent compositions. These cosmetic detergent compositions willgenerally contain, in addition to the aforesaid salt of a fatty acidalkanolamide-dicarboxylic acid monoester present in amounts varyingbetween 1 and 20%, preferably 3 to 10%, by weight, a quantity of waterin the range of about 10 to by weight, and the balance will be a memberof the group of synthetic organic detergents of the anionic, nonionic orcationic type.

The particular synthetic organic detergent, surfactant, soap or mixturethereof chosen for employment in the compositions of the preventinvention will be dependent upon the particular cosmetic preparationsought to be prepared. The compositions of the present inventionencompass shampoos, hair preparations such as conditioners and rinses,shaving preparations, especially aerosol shave preparation, skinconditioners and cleansing compositions, dishwashing detergentcompositions, hand lotions, bubblebath compositions and the like.

The synthetic organic detergents or surface-active agents which may beemployed in the compositions of the present invention may be selectedfrom a wide variety of water-soluble anionic, nonionic or cationicsurfactants such as are generally employed in aqueous cosmetic detergentor surfactant compositions which are meant to come into contact with theskin or hair.

Exemplary anionic materials are the water-soluble, straight and branchedchain alkyl aryl sulfonates, particularly the alkyl benzene sulfonates,wherein the alkyl group contains from about 8 to 15 carbon atoms, thelower alkyl aryl or hydrotropic sulfonates such as sodium xylenesulfonate; the olefin sulfonates such as those produced by sulfonating aC to C straight chain alphaolefin; hydroxy C to C alkyl sulfonates;water-soluble alkene disulfonates containing from about 10 to 24 carbonatoms; the normal and secondary higher alkyl detergents, particularlythose having about 8 to 15 carbon atoms in the alcohol residue such aslauryl or coconut fatty alcohol sulfate; sulfuric acid esters ofpolyhydric alcohols partially esterified With higher fatty acids such ascoconut oil monoglyceride monosulfate, coconut ethanolamide sulfate,lauric acid amide or taurine and the like; the various soaps or salts offatty acids containing from about 8 to 22, particularly 10 to 18, carbonatoms, such as the sodium, potassium, ammonium and lower alkanolamine,particularly mono-, diand triethanolamine salts of fatty acids such asstearic acid, oleic acid, coconut fatty acid, fatty acids derived frompalm oil, soybean oil, tallow and the like. Particularly preferredanionic surfactants include the fatty alcohol and ether alcohol sulfatesand the sodium salts of fatty acids containing from about 12 to 18carbon atoms.

Exemplary nonionic detergents which may be employed in the compositionsof the present invention are the polyalkylene oxide condensationproducts with a hydrophobic organic compound. The hydrophobic organicgroup usually contains from about 8 to 30 carbon atoms and is condensedwith from about to 50 alkylene oxide groups such as ethylene oxide,propylene oxide, butylene oxide, and the like. Specific condensationproducts include the polyoxyethylene ethers of alkyl phenols wherein thealkyl group contains from about 6 to 12 carbon atoms and containing fromabout 8 to 18 mols of ethylene oxide per mol of said alkyl phenols;polyalkylene oxide ethers of fatty alcohols such as lauryl, myristyl,cetyl, stearyl and oleyl alcohols, and C to C oxo alcohols, which arecondensed with from about 10 to 30 mols of ethylene oxide per mol ofsaid alcohols; polyoxyalkylene esters of organic acids such as thehigher fatty acids, rosin acids, tall oil acids and the like, saidesters containing from about 12 to 30 mols of ethylene oxide and about 8to 22 carbon atoms in the acyl group; polyalkylene oxides condensateswith higher fatty acid amides, such as the higher fatty acid primaryamides, monoand diethanolamides as well as condensates of higher fattyacid sulfonamides.

Further suitable nonionic surfactants are the higher fatty acidalkanolamides, such as the monoethanolamides, diethanolamides andisopropanolamides wherein the acyl radical has an average of from about10 to 18 carbon atoms. Examples are coconut fatty acid, capric, lauric,oleic and myristic diethanolamides and the correspondnigmonoethanolamides and isopropanolamides; the fatty tertiary amine oxideswhich may be represented by the general formula R R R N O wherein Rrepresents C to C alkyl such as decyl, dodecyl, tetradecyl, octadecyland the like and R and R represent methyl or ethyl.

Particularly preferred members of the above group of nonionicsurfactants include the fatty acid alkanolamides and thepolyoxyalkylene, particularly the ethylene oxide condensates thereof.

Exemplary cationic surfactants which may be employed in the compositionsof the present invention are quaternary ammonium salts having long chainhydrophobic radicals such as C to C alkyl radicals as exemplified byl-methyl-l-higher alkyl amido-ethyl-Z-higher alkyl imidazolinum saltswherein the alkyl groups have 10 to 20 carbon atoms, ethoxylated longchain fatty quaternary ammonium compounds, higher alkylbenzyldimethylammonium salts, higher alkyl isoquinolinium salts, di(higher alkyl) dimethylammonium salts, and the like. The anion of thewater-soluble quaternary ammonium compound is most usually a chloride ormethosulfate, but other ions may be used such as bromide, phosphate,dialkyl phosphate or acetate ions.

The aforesaid anionic, cationic and nonionic surfactants are generallypresent in amounts ranging from about 5 to 85%, by weight, dependingupon the particular cosmetic formulation prepared. Admixtures of theaforesaid may be employed so long as such admixtures are compatible anddo not cause precipitation or otherwise adversely affect the stabilityof the system.

Exemplary cosmetic detergent compositions are shampoos containing water,5-10% fatty amine oxide, 3-5% sodium fatty alcohol sulfate and about3-5% of said C C dicarboxylic acid-fatty acid alkanolamide monoestersalt; dishwashing liquids containing 1520% alkyl benzene sulfonate, 510%sulfated ethoxylated aliphatic alcohol, 310% hydrotropic sulfonate andfrom 5-10% of said C -C aliphatic dicarboxylic acid-fatty acidalkanolamide monoester salt; shampoo bars containing 60-70% mixed fattyacid soaps and 10-20% of said C -C aliphatic dicarboxylic acid-fattyacid alkanolamide monoester and the like.

Various supplemental materials may be added to the compositions of thepresent invention such as are generally employed in cosmeticpreparations. Exemplary are additives such as lanolin, ethoxylatedlanolin, glycerol and polyglycerols, lower alcohols such as ethanols,dyes, perfumes, antibacterial agents such as hexachlorophene,preservative agents such as formalin, sequestering agents such aswater-soluble phosphate compounds and the like.

The aqueous-based cosmetic detergent compositions of the presentinvention possess a number of highly significant advantages. Theyexhibit excellent emolliency when applied to the skin as hand lotions,skin cleansing compositions, shaving creams, or in the form ofdishwashing detergents. Emolliency refers to the desirable after-feelimparted to the skin and the conditioning and protective effects on theskin by the retention of natural greases or oils and the prevention andrelief of dryness. Shampoos formulated in accordance with the presentinvention impart an observable improved manageability and luster t0 thehair and emolliency to the scalp, and in addition, they have adiminished degreasing effect and are non-irritating to the scalp andskin. Moreover, compositions such as shaving preparations also showexcellent wetting and lathering properties and produce a soothing andnon-irritating effect upon the skin. Generally the compositions of thepresent invention have the capacity to reduce and suppress theirritating tendency of conventional detergents commonly employed indetergent compositions. Even in hard water, wetting and latheringproperties are not substantially diminished.

The invention is further illustrated by the following examples, whichare not to be considered as limitative of its scope. Percentages are byweight.

EXAMPLE I A shampoo is prepared containing the following ingredients:

Percent (a) Sodium lauryl sulfate 7 (b) Lauric diethanolamide 3 (c)Triethanolamine salt of the monoester of succinic acid and coconutmonoethanolamide 3 (d) Water 87 The above formulation is found to behigh lathering even in hard water, and non-drying to the hair and scalp.It is observed that after use, the hair has good manageability andluster, and does not require the use of a hair conditioning rinse.

EXAMPLE II (d) Ethanol 10 (e) Ammonium salt of the monoester of lauricmonoet-hanolamide and succinic acid 5 (f) Water 54 The above formulationis found not only to be nonirritating to the skin but produces anemollient effect on the skin after use. The identical composition,except for the ammonium lauric monoethanolamide monosuccinate isprepared for purposes of comparison and is found to produce a pronounceddrying effect on the hands with little or no emollient effect on theskin perceptible.

EXAMPLE 'III A soap bar is prepared by combining the followingingredients:

This soap bar forms a lather with water which is quite copious, similarto that of a shampoo lather and has a desirable after-feel on the skin.

EMMPLE IV A shampoo is prepared by combining the following ingredients:

Percent (a) Coconut diethanolamide 5.0 (b) Sodium lauryl sulfate 9.0

(c) Triethanolamine dodecyl benzene sulfonate 8.0

(d) Perfume 0.4 (e) Monosodium phosphate 0.6 (f) Sodium salt of themonoester of malonic acid with oleic isopropanolamide 2.0 (g) Water 75The product when applied to the hair significantly improvesmanageability with no drying eifect on the scalp.

EXAM'PLE V Example IV is repeated, except that for ingredient (f) thereis employed the ammonium salt of the monoester of glutaric acid withlauric diethanolamide and equivalent results are obtained.

EXAMPLE VI A various emollient hand lotion is prepared by combining thefollowing ingredients:

Percent (a) Lanolin 2.0 (b) Coconut diethanolamide 20.0 Sodium salt ofthe monoester of succinic acid with coconut butanolamide 5 .0 (d)Hexachlorop-hene 1.0 (e) Water 72 EXAMPLE VII A composition suitable asa skin-cleansing liquid or bubble-bath composition is prepared employingthe following components:

A shampoo is prepared by combining the following ingredients:

Percent (a) Triethanolammonium coconut sulfate 8.0

(b) Sodium alkyl (C -C sulfate 7.0

(c) Sodium t-octylphenl sulfonate 6.0 ((1) Potassium salt of themonoester of succinic acid and lauric monoethanolamide 1.0

(e) Water 78 6 EXAMPLE IX A hairdressing composition is prepared bycombining the following ingredients:

Percent (a) Polyoxyethylene ether of lauryl alcohol having 23oxyethylene units 5.0 (b) Lauric diethanolamide 6.0 (c) Lanolin 2.0 (d)Sodium salt of the monoester of succinic acid and coconutmonoethanolamide 5.0 (e) Glycerine 10.0 (f) Water 72 EXAMPLE X A shavingcream suitable for use in aerosol-type dispensers is prepared bycombining the following ingredients:

Percent (a) Glycerol 10.0 (b) Triethanolamine 4.0 (c) Stearic acid 4.5(d) Coconut fatty acids 1.5 (e) Glyceryl monostearate 5.0

(f) Triethanolamine salt of coconut monoethanolamide succinic acidmonoester 3.0 (g) Water 66.0 (h) Propellent(dichlorodifluoromethane-dichlorodifluoroethane mixture) 6.0

EXAMPLE XI An emollient skin cream is prepared by combining thefollowing ingredients:

Percent (a) Glyceryl monostearate 10.0 (b) Glycerol 15.0 (c) Cetyltrimethyl ammonium chloride 0.2

(d) Sodium salt of the monoester of succinic acid and coconutmonoethanolamide (e) Water 69.8

EXAMPLE XII A shampoo is prepared by combining the following ingredientsand is observed by the user to impart a greater What is claimed is:

1. An aqueous-based cosmetic detergent composition which consistsessentially of (a) from about 10% to 90%, by weight, of water; (b) fromabout 1% to 20%, by Weight, of a member of the group consisting ofammonium, C -C alkanolamine and alkali metal salts of monoesters of C -Csaturated, unsubstituted, aliphatic dicarboxylic acids with fatty acidmonoand di-alkanolamides wherein the alkanol portion contains up to 8carbon atoms; and (c) from 5% to by weight, of a member of the groupconsisting of synthetic anionic, nonionic and cationic organicdetergents and compatible mixtures of same with the proviso that said(0) ingredient is distinct from said (b) ingredient.

2. A composition according to claim 1 wherein said aliphaticdicarboxylic acid is succinic acid.

3. A compostion according to claim 1 wherein said fatty acidalkanolamide is a monoalkanolamide.

4. A composition according to claim 1 wherein said fatty acid containsfrom 10 to 18 carbon atoms.

5. A composition according to claim 1 wherein said salt is a sodiumsalt.

6. A composition according to claim 1 wherein said salts of saidmonoesters are present in an amount of from about 3% to about 10% byweight.

7. A composition according to claim 1 wherein said synthetic organicdetergent is a fatty alcohol sulfate.

8. A composition according to claim 1 wherein said synthetic organicdetergent is a member of the group consisting of fatty acid salts, fattyacid soaps and mixtures thereof.

9. A composition according to claim 1 wherein said synthetic organicdetergent is a fatty acid alkanolamide.

10. A composition according to claim 6 wherein said monoester salt isthe sodium salt of the monoester of succinic acid and coconutmonoethanolamide.

monoester salt is the triethanolamine salt of the monoester of succinicacid and lauric monoethanolamide.

References Cited UNITED STATES PATENTS 2,173,448 9/1939 Katzman et al.260404 2,733,212 1/ 1956 Epstein et a] 252-117 2,343,431 3/ 1944 Wellset a1 260-404 X 10 RICHARD D. LOVERING, Primary Examiner U.S. Cl. X.R.

252-90, 117, 134, 356, 527, 548, DIG. 5, DIG. 13;

11. A composition according to claim 6 wherein said 15 424-47 73

